Nomenclature of organic compounds

The name consists of three parts:

prefix nucleus sufix

Substituents Indicates No. of

Functional group
Location numbers carbons
Alkanes, alkenes and alkynes.
The name ends in –ane, -ene, -yne. If there are multiple bonds (double or triple bonds) their position is
indicated with a number. If there are more than one, suffixes such as enyne, diyne, diene, endiyne...
are used. For the numbering, double and triple bonds are considered together: In case of two identical
numerotations preference is given to the double bond. Cycloalkanes and cycloalkenes are named with
the nucleus preceded by the prefix cycle-.
1
CH3─CH=CH─C≡CH 3-penten-1-yne

1
HC≡C─CH=CH─CH=CH2 1,3-hexadien-5-yne

1
HC≡C─CH=CH─CH2─CH=CH2 3,6-heptadien-1-yne

Some have a common names

CH4 Methane CH2=CH2 Ethylene Benzene

CH3─CH3 Ethane CHΞCH Acetylene Toluene

CH3─CH2─CH3 Propane Phenol

CH3─(CH2)2─CH3 Butane Aniline

Alkyl, alkenyl or alkynyl radicals or groups originate by removing an H atom from an alkane. Their
termination is yl, enyl, ynyl ...

CH3─ Methyl CH3─(CH2)2─CH2─ Butyl

CH3─CH2─ Ethyl CH3─(CH2)3─CH2─ Pentyl

CH3─CH2─CH2── Propyl 3-pentenyl

Each compound can generate different radicals. They are named by giving the lowest possible
number to the radical carbon. Some radicals have a common name

propyl isopropyl

butyl sec-butyl isobutyl tert-butyl

 vinyl allyl Phenyl (C6H5-, Ph-) benzyl (C6H5CH2-)
Branched Compounds
1. Choose the chain with the highest number of carbons as the root chain.
• If there are two or more chains with the maximum number of carbons, choose the one with
more multiple bonds, if still in doubt choose the one with more double bonds and if more
than one option are possible, the one with more substituents.
• If there are still two or more chains in doubt, choose the one with the lowest locators.
2. Number the carbons of the root chain. If there are insaturations, give them the lowest posible
numbers (if both numerotations are identical give the lowest number to the double bonds). If there
are no multiple bonds give the first substituent the lowest number.
• If the first substituent is at the same distance from the two ends of the chain, give the
second substituent the lowest number:
• If numeration gives the same result in both senses, give the lowest number to the
substituent named first (in alphabetical order).
3. Name and number the substituents as radicals.
• Each substituent carries a locator.
• If there are two or more identical substituents use prefixes such as: di-, tri-, tetra-...
4. Build the name.
• Locators separated by commas, then a hyphen.
• Substituents in alphabetical order ignoring prefixes except iso, neo or cycle.
CH3 5-ethyl-2,6-dimethyloctane
CH3 • There is only an 8C chain
CH2 6
1 • Number from the left. Gives substituents
H 3C CH CH2 CH2 CH CH CH2 CH3 (2,5,6) better than (3,4,7).
2 5 8 • There is one ethyl (named first) and two
CH3 methyls (dimethyl)
CH3 CH3 CH3
CH
CH3 CH2
8 1 CH3 CH2 CH3
H 3C CH2 CH2 CH CH CH2 CH2 CH3
5 4 CH3 CH2 CH CH CH2 CH CH3
5 4 2 1
4-ethyl-5-methyloctane 7

Same numbering, lowest number to the one named 4-isobutyl-2,5-dimethylheptane

first
Three possibilities with 7C and 3 substituents.
Choose the one with lower locators

6,6-dimethyl-3-octyne
Lower numbering is given to multiple bonds, not
substituents

4-vinyloctane
NOT 3-propyl-1-heptene which is shorter
 3-ehynyl-1-heptene
NOT 3-butyl-1-penten-4-yne because it is longer

4-vinyl-1-hepten-5-yne
Because it is the longest

5-ethynyl-1,3,6-heptatriene
Lowest No. to double bond

Rings with substituents

The ring is always more important than the chains.
With an only substituent, no locator is needed; with two or more
the ring is numbered so that the lowest numbers are used.
(7-methyl-6-octen-3-yl)cyclopentane
If the substituents are different, give number 1 to the first one in
alphabetical order (1-ethyl-3-methylcyclohexane)

Ethylcyclobutane 1-ethyl-2-methylcyclohexane 1-sec-butyl-3-methylcyclohexane 1,2,4-triethylcyclopentane

1-methylcyclopentene 3-methylcycloheptene 1,6-dimethylcyclohexene 1-cyclodecen-3-yne

Aromatic hydrocarbons (arenes)

-With one substituent: e.g. propylbenzene
-With two substituents: Ortho (o), meta (m), para (p) nomenclature.
-With three or more substituents: locators and alphabetical order
-Polynuclear: naphthalene, anthracene and phenanthrene

tert-Butylbenzene ortho-dibromobenzene meta-dibromobenzene para-dibromobenzene

o-dibromobenzene m-dibromobenzene p-dibromobenzene
1,2-dibromobenzene 1,3-dibromobenzene 1,4-dibromobenzene

Naphthalene Antracene Phenantrene p-bromotoluene o-nitrophenol

 Main groups. Main chain always includes the main functional group

Group Formula Suffix Prefix

Carboxylic R-COOH Alcanoic Carboxy-

Acid Cycloalkanecarboxylic

Sulfonic R-SO3H Alkanesulfonic Sulfo-

Acid

Anhydride R-CO-O-CO-R' Alkanoic anhydride -

Ester R-CO-OR´ Alkyl Alkanoate (-O-CO-R) Alkanoyloxy-

Alkyl Cycloalkanecarboxylate
Cycloalkylcarbonyloxy-

Acid Halide R-CO-X Alcanoyl Halide Halocarbonyl-

Cycloalkanecarbonyl halide

Amide R-CO-NH Alkanamide (-NR-CO-R)

2
Cycloalkanecarboxamide Alkanamido-
(R )
2 Cycloalkanecarboxamido-
Sulfonamide R-SO -NH Alkanesulfonamide (-NR-SO -R)
2 2 2
(R ) Alkanesulfonamide-
2

Nitrile R-CN Alkanenitrile Cyano-

Cycloalkanecarbonitrile
Aldehyde R-CO-H Alkanal Oxo- o Formyl-
Cycloalkanecarbaldehide
Ketone R-CO-R' Alkanone Oxo-

Alcohol R-OH Alkanol Hydroxy-

Phenol Ar-OH Phenol Hydroxy-
Thyol R-SH Alkanethyol Sulfanyl-
Amine R-NH (R ) Alkanamine Amino-
2 2

Imine R-C=N-R' Alkanimine Imino-

Always as substituents
Ether R-O-R' - Alcoxy-
Sulfide R-S-R' - Alkylthyo-
Alkyl Halide R-X - Halo-
Nitrocompound R-NO - Nitro-
2
 Common names
1C 2C 3C* 4C* Ph
Acid HCOOH CH3COOH CH3CH2COOH CH3CH2CH2COOH PhCOOH
Formic acid Acetic acid Propionic acid Butiric acid Benzoic acid
Ester HCOOR CH3COOR CH3CH2COOR CH3CH2CH2COOR PhCOOR
Alkyl formate alkyl acetate alkyl propionate alkyl butirate Alkyl benzoate
Acid - CH3COCl CH3CH2COCl CH3CH2CH2COCl PhCOCl
chloride Acetyl chloride Propionyl chloride butyryl chloride Benzoyl chloride**
Amide HCONH2 CH3CONH2 CH3CH2CONH2 CH3CH2CH2CONH2 PhCONH2
Formamide Acetamide Propanamide Butanamide Benzamide
Nitrile HCN CH3CN CH3CH2CN CH3CH2CH2CN PhCN
Hydrogen cyanide. Acetonitrile Propanenitrile Butanenitrile Benzonitrile
Alde- HCHO CH3CHO CH3CH2CHO CH3CH2CH2CHO PhCHO
hyde Formaldehyde Acetaldehyde Propanal Butanal Benzaldehyde

* Common names are not accepted any more by IUPAC but still used in some books and by the industry
** Do not get confused with: Benzyl Chloride (PhCH2Cl) or Chlorobenzene (PhCl).

Examples
SO3 H
CH 3 O COOH
CH 3 CH CH 2 CH 2 C OH HOOC
COOH
4-methylpentanoic acid Br CH 3
3-bromocyclopentanecarboxylic acid 3-ethyl-6-methyloctanedioic acid 4-methylbenzenesulfonic
acid
p-toluenesulfonic acid

Heptanoic anhydride Acetic anhydride

3-methylbutyl pentanoate tert-butylcycloheptanecarboxylate 3-methylpentanoyl chloride

3-methylcyclopentanecarbonyl chloride N-ethylcyclobutanecarboxamide N,N-dimethylbenzamide

5-ethyl-7-methyloctanonitrile 1-naphthalenecarbonitrile 3-cyanobenzoyl chloride 2-bromocyclopentanecarbaldehyde

2-hexenedial 4-hexenal 4-formylheptanedioic acid 5-oxopentanoic acid

 More common names
CH3─CO─CH3 Acetone dimethylketone CH3─OH Methyl alcohol
Ph─CO─CH3 Acetophenone phenylmethylketone CH3CH2─OH Ethyl alcohol
Ph─CO─Ph Benzophenone diphenylketone Ph─CH2─OH Benzyl alcohol
Ph─NH2 Aniline CH2=CH─CH2─OH Allyl alcohol
Ph─CH2─NH2 Benzylamine CHX3 The Haloforms

Examples

4-(2-oxocyclohexyl)butanal cyclopentanol

2- methyl-2-pentanol 3-phenyl-2-butanol 1,4-pentanediol 7-hydroxy-4-methyl-2-heptanone phenol

1-naphthol 2-naphthol m-clorobenzoic acid 2-methylpropanamine cyclopentanamine

tert-butylamine cyclopentylamine

N-ethylbutilamine 6-methyl-3-heptanamine diphenylamine trimethylamine 1,3-propanediamine

N-ethyl-1-butanamine

2-aminomethylcyclohexanone p-toluidine ethoxycyclohexane

2-methylaminocyclohexanone Cyclohexylethyl ether

Methoxymethane 1,2-dimethoxyethane 2-ethoxypentane

Dimethyl ether

Nomenclature of molecules with stereogenic centers

Each stereogenic center is labeled with an R or an S.
To assign the letter proceed as follows (Cahn-Ingold-Prelog rules):
A.- Order the four atoms attached to the stereogenic center.
1. The atom with the highest atomic number has priority (with isotopes the one with the highest
mass)
 2. If two atoms attached to the stereogenic center are identical, priority is assigned considering the
atomic number of atoms attached to them
3. A multiple, double or triple bond is considered as two or three single bonds with identical atoms.

Rule 3
(red indicates that this atom is repeated, and the sequence finishes at this point)

O equivalent to O O equivalent to O C
C C O C C C O
H H OH O H
formyl carboxyl
C HH
equivalent to N C CH3 equivalent to
C N C H
C N C CH2 C C H
cyano N C CH
isopropenyl
CC
equivalent to C H equivalent to CC
C C C H
C C C CH C C
phenyl CH C
ethynyl
B.- Orient the molecule with the lowest priority group (4) back and visualize the relative
positions of the remaining three groups (priorities 1, 2 and 3).

C.- trace a circle going from 1 to 2 and 3.

If it goes in the clockwise direction the isomer is named R (Rectus).
If it goes in the counterclockwise direction the isomer is named S (Sinister)
Another way to do labelling if the 4th group is not backwards: Switching any two groups on a molecule
with a single stereogenic center, converts the molecule into its enantiomer.
H CH2CH3 COOH

Br Br H 2N
F H CH3 H 3C H
Cl

one change one change one change

1 2
2
Br CH2CH3 COOH

4 4
4 H H H NH2
Cl F 3 Br CH3 3
H3C
2 1 1
3

S R S

Application to double bonds with stereoisomerism

• The cis/trans nomenclature is not suitable in many cases. Then: priority is assigned separately to
the groups bonded to the two carbons of the double bond using the Cahn-Ingold-Prelog rules.
• If the highest priority groups are on the same side, it is called Z (for zusammen)
• If the highest priority groups are on opposite sides, it is called E (for entgegen)

(E)-3-methyl-2-pentene (Z)-3-methyl-2-pentene

PRACTICE EXCERCISES
01. Give the structure corresponding to each IUPAC name:

a) 1-methyl-4-(pentan-2-yl)cyclohexane e) 5-(but-3-ynyl)-5,6,6-trimethylcyclohexa-1,3-diene
b) 1-(2-bromoethyl)-4-methylcyclohexane f) 1,1-dichlorobuta-1,2-diene
c) 2-methyl-4-(1-propynyl)-2,5-heptadiene g) isopropylcyclobutane
d) 2-(2-methyl-5-phenylhexan-3-yl)naphthalene

02. Some of the following names are incorrect according to IUPAC rules. Say the correct name and
the structure in each case:

a) 2,3-diethybutane d) 2,4,5-trimethyl-3-propylheptane
b) 2,4,4-trichlorohexane e) 6-isopropyl-5-propyldecane
c) 1,4-diisopropylbutane f) 1,1,2-triphenylbutane
03.- Give the IUPAC name for the following compounds:

a) b) c)

d) e) f) g)

h) i) j) k)

04. Give the name for the following structures and indicate their functional groups and
their type (example: primary alcohol, carboxylic acid…)

COOCH2-CH2OH
O O
a) Br b) c)
H CH2OH
CHO

OH O COOH
d) e)
OCH3 NH2
CONH2

f) OH g)
H2N
CN
NO2

05. Give the IUPAC name for each compound

a) b)
COOCH3

Br OH
c) d) HO
O
H

e) HOOC COOH f)
COOH

g) h) O
O

06. Give the structure corresponding to each IUPAC name:

a) p-Nitrobenzoic acid
b) 3-Butenenitrile
c) m-Chlorobenzaldehyde
d) Methoxyethylene
 e) Tribenzylamine
f) N,N-Dimethylformamide

07. Which of the following compounds have Z/E stereochemistry?

a) 1,1-dichloroethylene d) 1-pentene
b) 2-butene e) 2-butenoic acid
c) 2-methyl-2-butene

08. Assign the correct configuration to the following alkenes:

a) b) c)
H3C CHO (CH3)2N COOH H3C H
C C C C C C
(CH3)2CH Cl H2NCH2 CH2SH Br CH3

09. Put an asterisk in all the seterogenic centers of the following molecules:

O
H CH3
N

O N
H
O
H H
HO OH HO

Thymidine Colesterol
OH
H3C OH N HO
OH H H
O
NH2
OH O N
OH O OH O O
Tetracycline Licorine

10. Label with R or S, these compounds:

a) b) c) d)
COOH H Ph
CH(CH3)2
Ph Cl H2N H2N
CN Ph C CH Cl CH3 CH=CH2
HO H
 More excercises with answers

O
1 2 3 4
H N

O N
H O
OH
5 6 7 8
H3C NH2
O2 N

OH
O O O2 N
9 10 11 12
O H
CN
CN

NO2 N O
CN
O 16 OH
13 14 15

OH O O
O O
17 18 19 20 Ph
OEt
O

a) Acetic anhydride j) Allylbenzylamine

b) 5-Methoxy-1-hexen-3-ol k) 2,3-Dimethyl-1,3-cyclohexadiene
c) p-Methoxyphenol l) 7,7-Dimethyl-1,3,5-octatriene
d) N-ethylaniline m) 7-Ethyl-3,3-dimethylcycloheptene
e) Acetonitrile n) 3-Ethynyl-7-vinyl-1,4-decadien-8-yne
f) Isopropyl benzoate o) 5-tert-Butyl-4-methyl-1,6-octadiyne
g) Phenoxyacetic acid p) p-Isopropyl (2-methyl-3-pentenyl) benzene
h) Benzoyl chloride q) 1-Allyl-2- (2-pentyl) -4-propylbenzene
i) Formaldehyde r) 1,1-Dimethyl-3-(pentan-3-yl)cyclopentane
 Answers:

O
1 2 3 4
H N

N,N-dimethylformamide (E)-5-allylnon-2-en-7-yne
2-ethyl-4-methyl-1- (E)-4-vinyloct-2-ene
vinylcyclohexane
O N
H O
OH
5 6 7 8
H3C NH2
O2 N
N,N,3-trimethylaniline acetamide
cyclopent-2-ene-1-carbaldehyde 4-nitrophenol

OH
O O O2 N
9 10 11 12
O H
CN
1-(2-hydroxycyclohexyl)propan-2- (E)-5-methylhept-3-enal CN 4-nitrobenzonitrile
one
2-(2-methoxycyclohexyl)acetonitrile
NO2 N O
CN 2-nitrobenzonitrile
O 16 OH
13 14 15

methoxycyclopropane N,N-dimethylaniline 3-vinylcyclopentane-1-

carboxylic acid

OH O O
O O
17 18 19 20 Ph
OEt
O 1-phenylpentane-1,3-dione
ethyl 3-oxobutanoate
(Z)-8-ethynyl-3,5-dimethylundec-3- 6-hydroxynonan-3-one
ene

O O
a) Acetic anhydride H 3C O CH3 k) 2,3-Dimethyl-1,3-cyclohexadiene

b) 5-Methoxy-1-hexen-3-ol OH O
l) 7,7-Dimethyl-1,3,5-octatriene
OH
c) p-Methoxyphenol
H3CO
m) 7-Ethyl-3,3-dimethylcycloheptene

d) N-ethylaniline NH

e) Acetonitrile H 3C C N n) 3-Ethynyl-7-vinyl-1,4-decadien-8-yne
O
f) Isopropyl benzoate
O
O o) 5-tert-Butyl-4-methyl-1,6-octadiyne

g) Phenoxyacetic acid O CH2 p) p-Isopropyl (2-methyl-3-pentenyl) benzene

OH
O
h) Benzoyl chloride
Cl
O q) 1-Allyl-2-(2-pentyl)-4-propylbenzene

i) Formaldehyde H H

j) Allilbenzylamine r)1,1-dimethyl-3-(pentan-3-yl)cyclopentane
HN